Synthesis, DFT and molecular docking of novel (Z)-4-bromo-N-(4-butyl-3 (quinolin-3-yl)thiazol-2(3H)-ylidene)benzamide as elastase inhibitor

BMC Chemistry

Research

Pervaiz Ali Channar¹  Qamar Abbas²  Muhammad Naeem Mustafa³  Aamer Saeed³  Syeda Abida Ejaz⁴  Mubashir Aziz⁴  Aisha A. Alsfouk⁵  Tuncer Hökelek⁶  Rabail Ujan⁷  Saira Afzal⁸  Tahira Shamim⁹ 

[1] Department of Basic Sciences and Humanities, Faculty of Information Sciences and Humanities, Dawood University of Engineering and Technology Karachi, 74800, Karachi, Pakistan;Department of Biology, College of Science, University of Bahrain, Sakhir Campus, 32038, Sakhir, Bahrain;College of Natural Sciences, Department of Biological Sciences, Kongju National University, 32588, Gongju, Republic of Korea;Department of Chemistry, Quaid-I-Azam University, 45320, Islamabad, Pakistan;Department of Pharmaceutical Chemistry, Faculty of Pharmacy, The Islamia University of Bahawalpur, 63100, Bahawalpur, Pakistan;Department of Pharmaceutical Sciences, College of Pharmacy, Princess Nourah bint Abdulrahman University, P.O Box 84428, 11671, Riyadh, Saudi Arabia;Department of Physics, Faculty of Engineering, Hacettepe University, 06800, Beytepe-Ankara, Ankara, Turkey;Dr. M. A. Kazi Institute of Chemistry, University of Sindh, Jamshoro, Pakistan;Faculty of Pharmacy, The University of Lahore, Lahore, Pakistan;University College of Conventional Medicine, Faculty of Medicine and Allied Health Sciences, The Islamia University of Bahawalpur, 63100, Bahawalpur, Pakistan;

关键词: Elastase;    Molecular docking;    Hirshfeld;    DFT studies;    Crystallography;   

DOI  :  10.1186/s13065-023-00985-4

 received in 2023-01-28, accepted in 2023-06-30,  发布年份 2023

来源: Springer

【 摘 要 】

A new compound, C23H20BrN3OS, containing a quinoline-based iminothiazoline with a thiazoline ring, was synthesized and its crystal and molecular structures were analyzed through single crystal X-ray analysis. The compound belongs to the triclinic system P − 1 space group, with dimensions of a = 9.2304 (6) Å, b = 11.1780 (8) Å, c = 11.3006 (6) Å, α = 107.146 (5)°, β = 93.701 (5)°, γ = 110.435 (6)°, Z = 2 and V = 1025.61 (12) Å3. The crystal structure showed that C–H···N and C–H···O hydrogen bond linkages, forming infinite double chains along the b-axis direction, and enclosing R22(14) and R22(16) ring motifs. The Hirshfeld surface analysis revealed that H…H (44.1%) and H…C/C…H (15.3%) interactions made the most significant contribution. The newly synthesized (Z)-4-bromo-N-(4-butyl-3 (quinolin-3-yl)thiazol-2(3H)-ylidene)benzamide, in comparison to oleanolic acid, exhibited more strong potential against elastase with an inhibition value of 1.21 µM. Additionally, the derivative was evaluated using molecular docking and molecular dynamics simulation studies, which showed that the quinoline based iminothiazoline derivative has the potential to be a novel inhibitor of elastase enzyme. Both theoretical and experimental findings suggested that this compound could have a number of biological activities.

【 授权许可】

CC BY   
© Springer Nature Switzerland AG 2023

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